Lithium Dialkylamide Mixed Aggregation: MNDO Computational Study of Salt and Solvent Dependencies

Journal of the American Chemical Society

Volumn 116, Issue 20, 1994, Pages 9187-9197

  Romesberg, Floyd E ^a   Collum, David B ^a  

^a Department of Obstetrics Gynecology   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000846077     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja00099a038     Document Type: Article

References (36)

1. Romesberg, F. E.; Collum, D. B. J. Am. Chem. Soc., following paper in this issue.
2. Mair, R. S.; Clegg, W.; O'Neil, P. A. J. Am. Chem. Soc. 1993, 775, 3388. See also: Engelhardt, L. M.; Jacobsen, G. E.; White, A. H.; Raston, C. L. Inorg. Chem. 1991, 30, 3978.
3. Williard, P. G.; Hintze, M. J. J. Am. Chem. Soc. 1987, 709, 5539.
4. Armstrong, D. R.; Barr, D.; Snaith, R.; Clegg, W.; Mulvey, R. E.; Wade, K.; Reed, D. J. Chem. Soc., Dalton Trans. 1987, 1071. Barr, D.; Snaith, R.; Clegg, W.; Mulvey, R. E.; Wade, K. J. Chem. Soc., Dalton Trans. 1987,2141. Armstrong, D. R.; Mulvey, R. E.; Walker, G. T.; Barr, D.; Snaith, R.; Clegg, W.: Reed, D. J. Chem. Soc, Dalton Trans. 1987, 617.
5. Reich, H. J.; Borst, J. P.; Dykstra, R. R.; Green, D. P. J. Am. Chem. Soc. 1993, 115, 8728.
6. Jackman, L. M.; Rakiewicz, E. F.; Benesi, A. J. Am. Chem. Soc. 1991, 113, 4101. Jackman,L. M.; Rakiewicz, E. F. J. Am. Chem. Soc. 1991, 113, 1202 and references cited therein.
7. Reich, H. J.; Green, D. P. J. Am. Chem. Soc. 1989, 711, 8729. Reich, H. J.; Green, D. P.; Phillips, N. H. J. Am. Chem. Soc. 1989, 777, 3444. Reich, H. J.; Borst, J. P. J. Am. Chem. Soc. 1991, 773, 1835. Reich, H. J.; Gudmundsson, B. O.; Dykstra, R. R. J. Am. Chem. Soc. 1992, 114, 7937. Reich, H. J.; Dykstra, R. R. J. Am. Chem. Soc. 1993, 775, 7041.
8. Jackman, L. M.; Chen, X. J. Am. Chem. Soc. 1992, 114, 403.
9. Romesberg, F. E.; Gilchrist, J. H.; Harrison, A. T.; Fuller, D. J.; Collum, D. B. J. Am. Chem. Soc. 1991, 773, 5751.
10. Romesberg, F. E.; Bernstein, M. P.; Fuller, D. J.; Harrison, A. T.; Collum, D. B. J. Am. Chem. Soc. 1993, 775, 3475.
11. Matsuda, H.; Hamatani, T.; Matsubara, S.; Schlosser, M. Tetrahedron 1988, 4, 2865. See also: Schlosser, M.; An, T. D. Angew. Chem., Int. Ed. Engl. 1981, 20, 1039. Schlosser, M.; Tarchini, C.; An, T. D.; Ruzziconi, R.; Bauer, P. J. Angew. Chem., Int. Ed. Engl. 1981, 20, 1041.
12. Williard, P. G.; Liu, Q.-Y. J. Am. Chem. Soc. 1993, 115, 3380.
13. For related structures, see: Stalke, D.; Klingebiel, U.; Sheldrick, G. M. J. Organomet. Chem. 1988, 344, 37. Dipple, K.; Klingebiel, U.; Kottke, T.; Pauer, F.; Sheldrick, G. M.; Stalke, D. Chem. Ber. 1990, 123, 237.
14. Bernstein, M. P.; Collum, D. B. J. Am. Chem. Soc. 1993, 115, 789.
15. Petasis, N. A.; Teets, K. A. J. Am. Chem. Soc. 1992, 114, 10328.
16. 24 For additional references, see: Eiermann, M.; Hafner, K. J. Am. Chem. Soc. 1992, 114, 135. Tsvetanov, Ch. B. Eur. Polym. J. 1979, 15, 503. Gill, J. B. Pure Appl. Chem. 1987,59,1127. Khan, I. M.; Hogen-Esch, T. E. J. Polym. Set., Polym. Chem. Ed. 1988, 26, 2553. Dotcheva, D.; Tsvetanov, Ch.; Lochmann, L. J. Polym. Sci., Polym. Chem. Ed. 1987, 25, 3005. Kocienski, P.; Barber, C. Pure Appl. Chem. 1990, 62, 1933. Pauer, F.; Rocha, J.; Stalke, D. Chem. Soc., Chem. Commun. 1991, 1477. Corstt, 3. Pure Appl. Chem. 1986,55,1133. Hojo, M.; Miyauchi, Y.; Nakatani, I.; Mizobuchi, T.; Imai, Y. Chem. Lett. 1990, 1035. Arnold, J.; Dawson, D. Y.; Hoffman, C. G. J. Am. Chem. Soc. 1993,115,2707. Bazan, G. C.; Schaefer, W. P.; Bercaw, J. E. Organometallics 1993,12,2126. Adler, H. J.; Lochmann, D. Makromolecules 1986,187, 1253. Hojo, M.; Fujime, C.; Yoneda, H. Chem. Lett. 1993, 37. Miyauchi, Y.; Hojo, M.; Moriyama, H.; Imai, Y. J. Chem. Soc., Faraday Trans. 1992, 3175. Gornitzka, H.; Stalke, D. Angew. Chem., Int. Ed. Engl. 1994, 33, 693.
17. Dewar, M. J. S.; Thiel, W. J. J. Am. Chem. Soc. 1977, 99, 4899; 4907.
18. Stewart, J. J. P. QCPE 581.
19. Kaufmann, E.; Schleyer, P. v. R. J. Am. Chem. Soc. 1984, 106, 1856. Sapse, A.-M.; Kaufmann, E.; Schleyer, P. v. R.; Gleiter, R. Inorg. Chem. 1984, 23, 1569.
20. Glaser, R.; Streitwieser, A., Jr. J. Mol. Struct. (JHEOCHEM) 1988, 163, 19.
21. Scano, P.; Thomson, C. J. Comput. Chem. 1991, 12, 172.
22. Considerable progress has been made in recent years to elucidate the structures of inorganic lithium salts. For leading references see, ref 21 and the following: Chabanel, H. Pure Appl. Chem. 1990, 62, 35.
23. Williard, P. G. Comprehensive Organic Synthesis; Pergamon: New York, 1991; Vol. 1, p 1. Boche, G. Angew. Chem., Int. Ed. Engl. 1989, 28, 277. Setzer, W. N.; Schleyer, P. v. R. Adv. Organomet. Chem. 1985, 24, 354.
24. Armstrong, D. R.; Barr, D.; Clegg, W.; Hodgson, S. M.; Mulvey, R. E.; Reed, D.; Snaith, R.; Wright, D. S. J. Am. Chem. Soc. 1989, 111, 4719. Dipple, K.; Klingebiel, U.; Nokemeyer, M.; Pauer, F.;Sheldrick,G. M. Angew. Chem., Int. Ed. Engl. 1988, 27, 1074. Engelhardt, L. M.; Jacobsen, G. E.; Junk, P. C.; Raston, C. L.; Skeleton, B. W.; White, A. H. J. Chem. Soc., Dalton Trans. 1988,1011. Armstrong, D. R.; Barr, D.; Clegg, W.; Mulvey, R. E.; Reed, D.; Snaith, R.; Wade, K. J. Chem. Soc., Chem. Commun. 1986, 869. Raston, C. L.; Skeleton, B. W.; Whitaker, C. R.; White, A. H. J. Chem. Soc, Dalton Trans. 1988, 987. Hoffmann, D.; Dorigo, A.; Schleyer, P. v. R.; Reif, H.; Stalke, D.; Sheldrick, G. M.; Weiss, E.; Geissler, M. In press.
25. See ref 8. For early suggestions that steric effects are major determinants of solvation, see: Settle, F. A.; Heggerty, M.; Eastham, J. F. J. Am. Chem. Soc. 1964, 86, 2076.
26. Williard, P. G.; Liu, Q.-Y. Unpublished results.
27. Homer, J. H.; Vera, M.; Grutzner, J. B. J.Org. Chem. 1986, 51, 4212.
28. McManus, S. P.; Capon, B. Neighboring Group Participation; Plenum Press: New York, 1976; p 58. See also: Bernardi, A.; Capelli, A. M.; Cassinari, A.; Comotti, A.; Gennari, C.; Scolastico, C. J. Org. Chem. 1992, 57, 7029. Bernardi, F.; Bongini, A.; Cainelli, G.; Robb, M.; Valli, G. S. J. Org. Chem. 1993, 58, 750.
29. Zimmerman, H. E.; Traxler, M. D. J. Am. Chem. Soc. 1957, 79, 1920.
30. Effects of HMPA on the chemistry of lithium amides: Fataftah, Z. A.; Kopka, I. E.; Rathke, M. W. J. Am. Chem. Soc 1980, 702, 3959. Fraser, R. R.; Mansour, T. S. Tetrahedron Lett. 1986, 27, 331. Kodomari, M.; Sawa, S.; Morozumi, K.; Ohkita, T. Nippon Kagaku Kaishi 1976, 301. Cuvigny, T.; Larcheveque, M.; Normant, H. Justus Liebigs Ann. Chem. 1975, 719. Reisdorf, D.; Normant, H. Organomet. Chem. Synth. 1972, 7, 375. Hosomi, A.; Araki, Y.; Sakurai, H. J. Am. Chem. Soc. 1982, 104, 2081. Cregge, R. J.; Hermann, J. L.; Lee, C. S.; Richman, J. E.; Schlessinger, R. H. Tetrahedron Lett. 1973, 2425. Shirai, R.; Tanaka, M.; Koga, K. J. Am. Chem. Soc. 1986, 70S, 543. Tsushima, K.; Araki, K.; Murai, A. Chem. Lett. 1989,1313. Tanaka, Y.; Tsujimoto, K.; Ohashi, M. Bull. Chem. Soc. Jpn. 1987,60,788. Kopka, I. E.; Fataftah, Z. A.; Rathke, M. W. J. Org. Chem. 1987, 52, 448.
31. Bunnage, M. E.; Davies, S. G.; Goodwin, C. J. J. Chem. Soc., Perkin Trans. 2 1993, 1375. Rudolf, K.; Hawkins, J. M.; Loncharich, R. J.; Houk, K. N. J. Org. Chem. 1988,53,3879. Hawkins, J. M.; Fu, G. C. J. Org. Chem. 1986, 57, 2820. Uyehara, T.; Shida, N.; Yamamoto, Y. J. Org. Chem. 1992, 57,3139. Hawkins,J.M.;Lewis,T.A.y.Ory.CAem.l992,57,2114. Uyehara, T.; Asao, N.; Yamamoto, Y. J. Chem. Soc., Chem. Commun. 1987, 1410. Asao.N.;Uyehara,T.;Yamamoto,Y. Tetrahedron 1988, 44,4173. Uyehara, T.; Shida, N.; Yamamoto, Y. J. Chem. Soc, Chem. Commun. 1989, 113. Liebeskind, L. S.; Welker, M. E.; Fengl, R. W. J. Am. Chem. Soc. 1986, 108, 6328. Davies, S. G.; Ichihara, O. Tetrahedron: Asymmetry 1991, 2, 183. Suzuki, I.; Kin, H.; Yamamoto, Y. J. Am. Chem. Soc. 1993, 775, 10139. Asao, N.; Uyehara, T.; Yamamoto, Y. Tetrahedron 1990, 46, 4563. Bellassoued, M.; Ennigrou, R.; Gandemar, M. J. Organomet. Chem. 1988, 338, 149. Uyehara, T.; Asao, N.; Yamamoto, Y. J. Chem. Soc, Chem. Commun. 1989, 753. Davies, S. G.; Ichihara, O. J. Chem. Soc, Chem. Commun. 1990,1554. Herrmann, J. L.; Kieczykowski, G. R.; Schlessinger, R. H. Tetrahedron Lett. 1973, 2433.
32. Leading references: Ashby, E. C.; Park, B.; Patil, G. S.; Gadru, K.; Gurumurthy, R. J. Org. Chem. 1993, 58, 424.
33. Nudelman, N. S. In The Chemistry of Double-Bonded Functional Groups; Patai, S., Ed.; Wiley: New York, 1989; Chapter 13, p 799.
34. Li, X.; Pan, H.; Jiang, X. Tetrahedron Lett. 1987, 28, 3699. Corriu, R. J. P.; Moreau, J. J. E.; Vernhet, C. Tetrahedron Lett. 1987, 28, 2963. Uyehara, T.; Asao, N.; Yamamoto, Y. Chem. Soc, Chem. Commun. 1987, 1410. Rathke, M. W.; Sullivan, D. Tetrahedron Lett. 1986,27,4249. Huisgen, R.; Mack, W. Chem. Ber. 1960, 93, 412. Kowalski, C.; Creary, X.; Rollin, A. J.; Burke, M. C. J. Org. Chem. 1978,43,2601. Meyers, A. I. J. Org. Chem. 1977, 42, 2653. Comins, D. L.; Brown, J. D.; Mantlo, N. B. Tetrahedron Lett. 1982, 23, 3979. Pez, G. P.; Galle, J. E. Pure Appl. Chem. 1985, 57, 1917. Petrov, A. A.; Kromer, V. A. Zh. Obshch. Khim. 1960, 30, 3890. Sanger, A. R. Inorg. Nucl. Chem. Lett. 1973, 9, 351. Tzschach, A.; Reiss, E. J. Organomet. 1967, S, 255. Liebeskind, L. S.; Welker, M. E.; Fengl, R. W. J. Am. Chem. Soc 1986, 70S, 6328.
35. Jackman, L. M.; Dunne, T. S. J. Am. Chem. Soc. 1985, 707, 2805. Pierre, J.-L.; Handel, H. Tetrahedron Lett. 1974, 2317. Loupy, A.; Seyden-Penne, J.; Tchoubar, B. Tetrahedron Lett. 1976, 1677. Buncel, E.; Dunn, E. J.; Bannard, R. A. B.; Purdon, J. G. J. Chem. Soc, Chem. Commun. 1984, 162. Chang, C. J.; Kiesel, R. F.; Hogen-Esch, T. L. J. Am. Chem. Soc. 1973, 95, 8446. Loupy, A.; Seyden-Penne, J. Tetrahedron 1980, 36, 1937.
36. Martin, V. A.; Perron, F.; Albizati, K. F. Tetrahedron Lett. 1990, 31, 301. Martin, V. A.; Murray, D. H.; Pratt, N. E.; Zhao, Y.-b.; Albizati, K. F. J. Am. Chem. Soc. 1990, 112, 6965. Carpenter, A. J.; Chadwick, D. J. J. Org. Chem. 1985, 50, 4362. Snieckus, V. Chem. Rev. 1990, 90, 879. Estermann, H.; Seebach, D. Helv. Chim. Acta 1988, 77, 1824. Ohta, H.; Matsumoto, S.; Sugai, T. Tetrahedron Lett. 1990, 31, 2895. Esswein, A.; Betz, R.; Schmidt, R. Helv. Chim. Acta 1989, 72, 213. Block, E.; Gernon, M.; Kang, H.; Ofori-Okai, G.; Zubieta, J. Inorg. Chem. 1991, 30, 1736. Bollinger, P.; Copper, P.; Gubler, H. U.; Leutwiler, A.; Payne, T. Helv. Chim. Acta 1990, 73, 1197.